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Remote C–H Functionalization via Selective Hydrogen Atom Transfer

Synthesis · 2018 · Vol. 50(08) · pp. 1569–1586
David A. NagibLeah M. StatemanKohki M. Nakafuku

Abstract

The selective functionalization of remote C-H bonds via intramolecular hydrogen atom transfer (HAT) is transformative for organic synthesis. This radical-mediated strategy provides access to novel reactivity that is complementary to closed-shell pathways. As modern methods for mild generation of radicals are continually developed, inherent selectivity paradigms of HAT mechanisms offer unparalleled opportunities for developing new strategies for C-H functionalization. This review outlines the history, recent advances, and mechanistic underpinnings of intramolecular HAT as a guide to addressing ongoing challenges in this arena.

Radical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesChemistryRadicalSurface modificationIntramolecular forceHydrogen atomAlkoxy groupPhotochemistryDiradicalReactivity (psychology)Stereochemistry

Funding

  • American Chemical Society Petroleum Research Fund
  • National Institute of General Medical Sciences
Citations
456
FWCI
24.55
field-weighted impact
References
150
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100%
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References
Visible light photoredox catalysis: applications in organic synthesis
Chemical Society Reviews · 2010 · 4,059 citations
CH Bond Functionalization: Emerging Synthetic Tools for Natural Products and Pharmaceuticals
Angewandte Chemie International Edition · 2012 · 2,943 citations
Organic Photoredox Catalysis
Chemical Reviews · 2016 · 6,022 citations
Photoredox Catalysis in Organic Chemistry
The Journal of Organic Chemistry · 2016 · 3,057 citations
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